EP0072238B1 - Dérivés de pyridazinone, leur préparation et leur utilisation dans des compositions pour l'agriculture et le traitement des graines et des plantes - Google Patents
Dérivés de pyridazinone, leur préparation et leur utilisation dans des compositions pour l'agriculture et le traitement des graines et des plantes Download PDFInfo
- Publication number
- EP0072238B1 EP0072238B1 EP82304197A EP82304197A EP0072238B1 EP 0072238 B1 EP0072238 B1 EP 0072238B1 EP 82304197 A EP82304197 A EP 82304197A EP 82304197 A EP82304197 A EP 82304197A EP 0072238 B1 EP0072238 B1 EP 0072238B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- formula
- compound
- halogen atom
- pyridazinone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title description 14
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 131
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 46
- 125000005843 halogen group Chemical group 0.000 claims description 38
- 230000000855 fungicidal effect Effects 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000000417 fungicide Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 229920002866 paraformaldehyde Polymers 0.000 claims description 10
- 230000002140 halogenating effect Effects 0.000 claims description 9
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- MDPAOBITXXTOPU-UHFFFAOYSA-N 6-(3-bromophenyl)-2-(hydroxymethyl)pyridazin-3-one Chemical compound C1=CC(=O)N(CO)N=C1C1=CC=CC(Br)=C1 MDPAOBITXXTOPU-UHFFFAOYSA-N 0.000 claims description 3
- OFGHCWFAKYCFHS-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-2-(hydroxymethyl)pyridazin-3-one Chemical compound C1=CC(=O)N(CO)N=C1C1=CC=C(Cl)C(Cl)=C1 OFGHCWFAKYCFHS-UHFFFAOYSA-N 0.000 claims description 2
- WSGZVSGEIPZSSE-UHFFFAOYSA-N 6-(3,5-dichloro-4-methylphenyl)-2-(hydroxymethyl)pyridazin-3-one Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NN(CO)C(=O)C=C1 WSGZVSGEIPZSSE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 230000002538 fungal effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- -1 N-substituted methyldihydro-pyridazinone Chemical class 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 240000007594 Oryza sativa Species 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000002689 soil Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 0 Cc1c(C)c(*)cc(C(N2)=**(*)C2=O)c1 Chemical compound Cc1c(C)c(*)cc(C(N2)=**(*)C2=O)c1 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 244000053095 fungal pathogen Species 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- BMMQDXFSGTYZPE-UHFFFAOYSA-N 3-(3-bromophenyl)-1h-pyridazin-6-one Chemical compound BrC1=CC=CC(C2=NNC(=O)C=C2)=C1 BMMQDXFSGTYZPE-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- IZVSKWYEIZZAGN-UHFFFAOYSA-N 6-(3-bromophenyl)-2-(chloromethyl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCl)N=C1C1=CC=CC(Br)=C1 IZVSKWYEIZZAGN-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000918585 Pythium aphanidermatum Species 0.000 description 3
- 241000813090 Rhizoctonia solani Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 231100000989 no adverse effect Toxicity 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- SKLOMJDBOQJPJM-UHFFFAOYSA-N 2-(chloromethyl)-6-(3,4-dichlorophenyl)pyridazin-3-one Chemical compound C1=CC(=O)N(CCl)N=C1C1=CC=C(Cl)C(Cl)=C1 SKLOMJDBOQJPJM-UHFFFAOYSA-N 0.000 description 2
- ZUPUQHOCIJFGQY-UHFFFAOYSA-N 2-(chloromethyl)-6-(3,5-dichloro-4-methoxyphenyl)pyridazin-3-one Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1C1=NN(CCl)C(=O)C=C1 ZUPUQHOCIJFGQY-UHFFFAOYSA-N 0.000 description 2
- QOCFBCXMWCJNPR-UHFFFAOYSA-N 2-[(4-chloroanilino)methyl]-6-(3,4-dichlorophenyl)pyridazin-3-one Chemical compound C1=CC(Cl)=CC=C1NCN1C(=O)C=CC(C=2C=C(Cl)C(Cl)=CC=2)=N1 QOCFBCXMWCJNPR-UHFFFAOYSA-N 0.000 description 2
- ZVEKBPHAAOLRKH-UHFFFAOYSA-N 2-[(cyclohexylamino)methyl]-6-(3,4-dichlorophenyl)pyridazin-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=NN(CNC2CCCCC2)C(=O)C=C1 ZVEKBPHAAOLRKH-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ROGGOQJSJXAVJH-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-2-(morpholin-4-ylmethyl)pyridazin-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=NN(CN2CCOCC2)C(=O)C=C1 ROGGOQJSJXAVJH-UHFFFAOYSA-N 0.000 description 2
- XOBKKZCZKAGNFL-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-2-(piperidin-1-ylmethyl)pyridazin-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=NN(CN2CCCCC2)C(=O)C=C1 XOBKKZCZKAGNFL-UHFFFAOYSA-N 0.000 description 2
- HPLKITRDHVYWMZ-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-2-[(4-methylanilino)methyl]pyridazin-3-one Chemical compound C1=CC(C)=CC=C1NCN1C(=O)C=CC(C=2C=C(Cl)C(Cl)=CC=2)=N1 HPLKITRDHVYWMZ-UHFFFAOYSA-N 0.000 description 2
- COJAIEYEDHTUJV-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-2-[[4-[[3-(3,4-dichlorophenyl)-6-oxopyridazin-1-yl]methyl]piperazin-1-yl]methyl]pyridazin-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=NN(CN2CCN(CN3C(C=CC(=N3)C=3C=C(Cl)C(Cl)=CC=3)=O)CC2)C(=O)C=C1 COJAIEYEDHTUJV-UHFFFAOYSA-N 0.000 description 2
- ZXYWONBPLMIQNS-UHFFFAOYSA-N 6-(3,5-dichloro-4-methylphenyl)-2-(morpholin-4-ylmethyl)-4,5-dihydropyridazin-3-one Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C(CCC1=O)=NN1CN1CCOCC1 ZXYWONBPLMIQNS-UHFFFAOYSA-N 0.000 description 2
- VYRDHHQCEPTJDX-UHFFFAOYSA-N 6-(3,5-dichloro-4-methylphenyl)-2-(morpholin-4-ylmethyl)pyridazin-3-one Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NN(CN2CCOCC2)C(=O)C=C1 VYRDHHQCEPTJDX-UHFFFAOYSA-N 0.000 description 2
- ZWLWJIHOPBBNSD-UHFFFAOYSA-N 6-(3-bromophenyl)-2-(hydroxymethyl)-4,5-dihydropyridazin-3-one Chemical compound C1CC(=O)N(CO)N=C1C1=CC=CC(Br)=C1 ZWLWJIHOPBBNSD-UHFFFAOYSA-N 0.000 description 2
- SMTOEWYAQCSTKR-UHFFFAOYSA-N 6-(3-bromophenyl)-2-(morpholin-4-ylmethyl)-4,5-dihydropyridazin-3-one Chemical compound BrC1=CC=CC(C=2CCC(=O)N(CN3CCOCC3)N=2)=C1 SMTOEWYAQCSTKR-UHFFFAOYSA-N 0.000 description 2
- UPSWAMUWMBSGGA-UHFFFAOYSA-N 6-(3-bromophenyl)-2-(morpholin-4-ylmethyl)pyridazin-3-one Chemical compound BrC1=CC=CC(C2=NN(CN3CCOCC3)C(=O)C=C2)=C1 UPSWAMUWMBSGGA-UHFFFAOYSA-N 0.000 description 2
- VMAGKLFSSOKATJ-UHFFFAOYSA-N 6-(3-bromophenyl)-2-(piperidin-1-ylmethyl)pyridazin-3-one Chemical compound BrC1=CC=CC(C2=NN(CN3CCCCC3)C(=O)C=C2)=C1 VMAGKLFSSOKATJ-UHFFFAOYSA-N 0.000 description 2
- BPSHUVPMDYKCDZ-UHFFFAOYSA-N 6-(3-bromophenyl)-2-[[butyl(methyl)amino]methyl]pyridazin-3-one Chemical compound C1=CC(=O)N(CN(C)CCCC)N=C1C1=CC=CC(Br)=C1 BPSHUVPMDYKCDZ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- 235000009852 Cucurbita pepo Nutrition 0.000 description 2
- 240000001980 Cucurbita pepo Species 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 240000002024 Gossypium herbaceum Species 0.000 description 2
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 244000061458 Solanum melongena Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- XXXFZKQPYACQLD-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl acetate Chemical compound CC(=O)OCCOCCO XXXFZKQPYACQLD-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- SSXISMDPFQHCMU-UHFFFAOYSA-N 2-(chloromethyl)-6-(3,5-dibromo-4-methylphenyl)pyridazin-3-one Chemical compound C1=C(Br)C(C)=C(Br)C=C1C1=NN(CCl)C(=O)C=C1 SSXISMDPFQHCMU-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- VIHPFQJBJHYMII-UHFFFAOYSA-N 2-[(propan-2-ylamino)methyl]pyridazin-3-one Chemical compound C(C)(C)NCN1N=CC=CC1=O VIHPFQJBJHYMII-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- VURUNMWLBDYAMB-UHFFFAOYSA-N 2-butylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CCCC)=CC=C21 VURUNMWLBDYAMB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- PUWMHJMSNXPBBW-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1h-pyridazin-6-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=NNC(=O)C=C1 PUWMHJMSNXPBBW-UHFFFAOYSA-N 0.000 description 1
- ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical class O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 description 1
- ZGJBHRJDZBLCQH-UHFFFAOYSA-N 6-(3,5-dichloro-4-methoxyphenyl)-2-(morpholin-4-ylmethyl)pyridazin-3-one Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1C1=NN(CN2CCOCC2)C(=O)C=C1 ZGJBHRJDZBLCQH-UHFFFAOYSA-N 0.000 description 1
- BIHLLIKYJRTGMO-UHFFFAOYSA-N 6-(3,5-dichloro-4-methylphenyl)-2-(hydroxymethyl)-4,5-dihydropyridazin-3-one Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NN(CO)C(=O)CC1 BIHLLIKYJRTGMO-UHFFFAOYSA-N 0.000 description 1
- WYAPLCPYTQRJLA-UHFFFAOYSA-N 6-(3,5-dichloro-4-methylphenyl)-2-[(4-phenylpiperazin-1-yl)methyl]pyridazin-3-one Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NN(CN2CCN(CC2)C=2C=CC=CC=2)C(=O)C=C1 WYAPLCPYTQRJLA-UHFFFAOYSA-N 0.000 description 1
- BJIMPDNXOLKBTI-UHFFFAOYSA-N 6-(3,5-dichloro-4-methylphenyl)-2-methylpyridazin-3-one Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NN(C)C(=O)C=C1 BJIMPDNXOLKBTI-UHFFFAOYSA-N 0.000 description 1
- KKOKGTNJYJSSTM-UHFFFAOYSA-N 6-(3-bromo-4-fluorophenyl)-2-(chloromethyl)pyridazin-3-one Chemical compound C1=C(Br)C(F)=CC=C1C1=NN(CCl)C(=O)C=C1 KKOKGTNJYJSSTM-UHFFFAOYSA-N 0.000 description 1
- DQQKJLGZDQHGKW-UHFFFAOYSA-N 6-(3-bromo-4-fluorophenyl)-2-(piperidin-1-ylmethyl)pyridazin-3-one Chemical compound C1=C(Br)C(F)=CC=C1C1=NN(CN2CCCCC2)C(=O)C=C1 DQQKJLGZDQHGKW-UHFFFAOYSA-N 0.000 description 1
- FYKYNRLNUZUTEN-UHFFFAOYSA-N 6-(3-bromophenyl)-2-(pyrrolidin-1-ylmethyl)-4,5-dihydropyridazin-3-one Chemical compound BrC1=CC=CC(C=2CCC(=O)N(CN3CCCC3)N=2)=C1 FYKYNRLNUZUTEN-UHFFFAOYSA-N 0.000 description 1
- MQGKSALRHGAIFM-UHFFFAOYSA-N 6-(3-bromophenyl)-2-(pyrrolidin-1-ylmethyl)pyridazin-3-one Chemical compound BrC1=CC=CC(C2=NN(CN3CCCC3)C(=O)C=C2)=C1 MQGKSALRHGAIFM-UHFFFAOYSA-N 0.000 description 1
- RSDOIQFUHXPUPQ-UHFFFAOYSA-N 6-(3-bromophenyl)-2-methylpyridazin-3-one Chemical compound C1=CC(=O)N(C)N=C1C1=CC=CC(Br)=C1 RSDOIQFUHXPUPQ-UHFFFAOYSA-N 0.000 description 1
- WUXBHLHMPAMCJT-UHFFFAOYSA-N 6-(3-chloro-4-methoxyphenyl)-2-[(4-methylpiperazin-1-yl)methyl]pyridazin-3-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NN(CN2CCN(C)CC2)C(=O)C=C1 WUXBHLHMPAMCJT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000478345 Afer Species 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- RZYWRVKFWLLGDI-UHFFFAOYSA-N C1C(=O)N(CNC)N(CNC)C(C=2C=C(Cl)C(Cl)=CC=2)=C1 Chemical compound C1C(=O)N(CNC)N(CNC)C(C=2C=C(Cl)C(Cl)=CC=2)=C1 RZYWRVKFWLLGDI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 108010076119 Caseins Proteins 0.000 description 1
- 241000426497 Chilo suppressalis Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 239000004859 Copal Substances 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 229920002871 Dammar gum Polymers 0.000 description 1
- 239000004860 Dammar gum Substances 0.000 description 1
- 208000001840 Dandruff Diseases 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000782205 Guibourtia conjugata Species 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241001617088 Thanatephorus sasakii Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- DWHOIYXAMUMQTI-UHFFFAOYSA-L disodium;2-[(1-sulfonatonaphthalen-2-yl)methyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC2=CC=CC=C2C(S(=O)(=O)[O-])=C1CC1=CC=C(C=CC=C2)C2=C1S([O-])(=O)=O DWHOIYXAMUMQTI-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000021332 kidney beans Nutrition 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- IXYACKYHUWCLAM-UHFFFAOYSA-M sodium;2-ethylhex-1-ene-1-sulfonate Chemical compound [Na+].CCCCC(CC)=CS([O-])(=O)=O IXYACKYHUWCLAM-UHFFFAOYSA-M 0.000 description 1
- AZXQLMRILCCVDW-UHFFFAOYSA-M sodium;5-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(C(C)C)=CC=CC2=C1S([O-])(=O)=O AZXQLMRILCCVDW-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
Definitions
- the present invention relates to a series of new pyridazinone derivatives which have fungicidal activity, and provides a method of preparing these compounds and agricultural fungicidal compositions containing them.
- Japanese Examined Patent Publication No 12386/60 describes a method of producing a N-substituted methyldihydro-pyridazinone represented by the formula: (wherein R represents an alkyl group, an aromatic group or a substituted aromatic group and Y represents a hydroxy group or a halogen atom) which is characterized by reacting a 4,5-dihydropyridazinone derivative represented by the formula: (wherein R is as defined above) with formaldehyde to effect condensation and, if necessary, by further treating the obtained product to convert the hydroxy group with a halogenating agent.
- the derivatives are used as intermediates for the preparation of insecticides by esterification with phosphoric acids.
- Spanish Patent No. 467,728 discloses processes for preparing some of the same compounds as are disclosed in United Kingdom Patent Specification No. 1,533,010 and also discloses a number of previously unknown, but related compounds, including some in which R" in the above formula represents an alkyl group.
- United Kingdom Patent Specification No. 2,047,702A disclosed a series of compounds similar to those of the above formula but in which either the carbonyl group on the pyridazine ring has been replaced by a N-substituted carbamoyloxy group (or the sulphur analogue in which one or both of the oxygen atoms in the carbamoyloxy group has been replaced by a sulphur atom) or in which there is an alkyl-, aryl- or aralkyl- oxy (or thio)-carbonyl group on the nitrogen atom adjacent the pyridazinone carbonyl group.
- the new pyridazinone derivatives of the present invention are those compounds which may be represented by formula (I): in which:
- the invention also provides a process for preparing the compounds of the invention in which a compound of formula (II): (in which A, R 1 , R 2 and R 3 are as defined above) is reacted with formaldehyde to give a compound of formula (la): (in which A, R 1 , R 2 and R 3 are as defined above) and, if necessary, this compound of formula (la) is reacted with a halogenating agent, an amine or piperazine, to give the desired compound of formula (I).
- the invention still further provides an agricultural fungicidal composition
- a fungicide in admixture with an agriculturally acceptable carrier or diluent, wherein the fungicide is at least one compound of formula (I).
- the invention also provides a method of preventing or controlling fungal attack on seeds or growing plants by applying to the seeds or growing plants an effective amount of a fungicide, wherein the fungicide comprises at least one compound of formula (I).
- R 1 , R 2 , R 3 or Y represents a halogen atom
- this may be a chlorine, bromine, fluorine or iodine atom, but is preferably a chlorine or bromine atom.
- R 2 or R 4 represents an alkyl group
- it is a lower alkyl group, which may be a straight or branched chain alkyl group, and has from 1 to 4 carbon atoms, for example a methyl, ethyl, propyl, isopropyl, butyl or isobutyl group; of these, the methyl and ethyl, especially the methyl groups are preferred.
- R 2 represents an alkoxy group
- this is a lower alkoxy group, which may be a straight or branched chain group, and has from 1 to 4 carbon atoms.
- examples of such groups include the methoxy, ethoxy, propoxy, isopropoxy, butoxy and isobutoxy groups, of which the methoxy and ethoxy, especially the methoxy, groups are preferred.
- Y represents an alkylamino or dialkylamino group
- the or each alkyl group may be a straight or branched chain group, and has from 1 to 8 carbon atoms, for example a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, heptyl, octyl or 2-ethylhexyl group.
- Y represents an alkenylamino or a dialkenylamino group
- the or each alkenyl group is a lower alkenyl group, which may be a straight or branched chain group, and has 3 or 4 carbon atoms.
- Examples of such groups include the allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl and 2-butenyl groups of which the allyl group is preferred.
- Y represents an anilino group having one or two substituents
- the substituents may be halogen atoms (for example, chlorine, bromine, fluorine or iodine atoms) or alkyl groups, preferably lower alkyl groups (for example methyl, ethyl, propyl or isopropyl groups).
- substituents there are two substituents, these may be the same of different, for example two halogen atoms, two alkyl groups or one halogen atom and one alkyl group.
- Y represents a cycloalkylamino group
- the cycloalkyl group is a 5, 6 or 7 membered cycloalkyl group, for example a cyclohexyl, cyclopentyl or cycloheptyl group, of which the cyclohexyl group is preferred.
- the compounds of formula (I) may be prepared by the following processes.
- the amount of formaldehyde is preferably equimolar or greater with respect to the compound of formula (II).
- the reaction is preferably carried out in the presence of a solvent, the nature of which is not critical, provided that it has no adverse effect upon the reaction.
- suitable solvents include alcohols (such as methanol, ethanol, isopropanol or butanol) and mixtures of one or more of these alcohols with water.
- the reaction is also preferably carried out in the presence of a small quantity of catalyst, which is preferably an inorganic base (such as sodium carbonate, sodium bicarbonate, potassium carbonate, sodium hydroxide, potassium hydroxide or calcium hydroxide) or a mineral acid (for example, sulphuric acid, hydrochloric acid or phosphoric acid).
- the temperature at which the reaction is carried out is not critical and may vary over a wide range, however, we have found that it is generally convenient to carry out the reaction at the reflux temperature of the solvent employed.
- Suitable halogenating agents include thionyl chloride, thionyl bromide and phosphorus oxychloride.
- the amount of halogenating agent is preferably at least equimolar with respect to the compound of formula (la).
- the reaction may be carried out in the presence or absence of a solvent.
- a solvent such as benzene, toluene and xylene.
- the halogenation reaction is preferably effected with heating, but the reaction temperature is not critical, and we therefore normally prefer to carry out the reaction at the reflux temperature of the solvent employed or of the reaction mixture.
- the compounds of formula (lb) by reacting the compound of formula (II) directly with the halogenating agent and paraformaldehyde.
- the reaction is preferably carried out in the presence of a solvent (e.g. an aromatic hydrocarbon such as benzene, tolune or xylene) at a temperature from ambient to reflux.
- a solvent e.g. an aromatic hydrocarbon such as benzene, tolune or xylene
- the amount of paraformaldehyde is preferably from 1 to 5 moles and that of halogenating agent is preferably from 1 to 10 moles, both per mole of compound (II).
- This reaction is preferably effected in the presence of a solvent, the nature of which is not critical, provided that it has no adverse effect on the reaction.
- suitable solvents include: alcohols, such as methanol, ethanol, isopropanol or butanol; ethers, such as diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran; aromatic hydrocarbons, such as benzene, toluene or xylene; ketones, such as acetone or methyl ethyl ketone; halogenated hydrocarbons, such as methylene chloride, ethylene chloride, chloroform or carbon tetrachloride.
- reaction temperature is not critical and may vary over a wide range; for convenience, we normally prefer to carry out the reaction at a temperature of from room temperature to the reflux temperature of the solvent employed.
- the molar ratio of the compound of formula (la) or (lb) to the amine HY' is preferably from 1:1 to 1:5, although, if the amine is a secondary amine, it may be employed in an amount greater 5 moles per mole of the compound of formula (la) or (lb).
- the reaction is preferably effected in the presence of an acid-binding agent, for example an inorganic base (such as sodium carbonate, potassium carbonate or sodium bicarbonate) or an organic base (such as pyridine or triethylamine).
- an acid-binding agent for example an inorganic base (such as sodium carbonate, potassium carbonate or sodium bicarbonate) or an organic base (such as pyridine or triethylamine).
- compounds of formula (Ic) can be prepared by heating the compound of formula (II) with formaldehyde (preferably in the form of formalin or paraformaldehyde) and the amine of formula HY', in the presence of a solvent.
- formaldehyde preferably in the form of formalin or paraformaldehyde
- the solvents and amounts of reagents may be chosen from those suggested when the reactions are carried out separately.
- the reaction temperature may range from ambient to reflux temperature.
- the molar ratio of compound (II), formaldehyde and piperazine is preferably 2:2:1.
- the desired products may be isolated by conventional means and, if necessary, further purified, for example, by recrystallisation and/or chromatography, particularly column chromatography.
- the compounds of the present invention may be employed as agricultural fungicides and show a preventive and curvative effect against plant diseases, without damaging the host plants. They have better systemic action (i.e. penetrating of the compounds into and translocation of the compounds in the plant body) than do the compounds of United Kingdom Patent Specification 1,553,010 and Spanish Patent Specification No. 467,728, and have a greater chemical stability than do the compounds of United Kingdom Patent Specification No. 2,047,702A.
- sheath blight which is a very serious disease attacking rice plants
- they are preferably employed in the form of a spray, particularly a foliar spray, or are applied, dissolved or dispersed in water, to the soil surface.
- a spray particularly a foliar spray
- They also effectively control damping-off of various crops, such as beet, cotton plants and plants of the gourd family, which disease is caused by pathogenic fungi of the class Rhizoctonia.
- the compounds of the invention do not exhibit any phytotoxicity to such plants as rice plants, tomato plants, potatoes, cotton plants, aubergine plants, cucumbers and kidney beans. Moreover, they may be used effectively as fungicides in orchards, non-crop land and forests.
- the compounds of the invention may be formulated as preparations of the type commonly employed as agricultural fungicides, for example powdery dusts, coarse dusts, fine granules, coarse granules, wettable powders, emulsifiable concentrates, aqueous liquids, water-soluble powders and oil suspensions, by mixing them with a carrier and, if required, with other auxiliary agents.
- the carrier employed may be natural or synthetic and organic or inorganic; it is mixed with the active compound to assist that compound to reach the material to be treated and to make it easier to store, transport or handle the active compound.
- Suitable solid carriers are: inorganic substances, such as clays (examples of which are kaolinite, montmorillonite or attapulgite), talc, mica, pyrophyllite, pumice, vermiculite, gypsum, calcium carbonate, dolomite, diatomaceous earth, magnesium carbonate, apatite, zeolite, silicic anhydride and synthetic calcium silicate; vegetable organic substances, such as soybean meal, tobacco powder, walnut powder, wheat flour, wood meal, starch and crystalline cellulose; synthetic or natural high molecular weight polymers, such as cumarone resins, petroleum resins, alkyd resins, polyvinyl chloride, polyalkylene glycols, ketone resins, ester gums, copal gum and dammar gum; waxes, such as carnauba wax and beeswax; or urea.
- inorganic substances such as clays (examples of which are kaolinite, montmorillonite
- liquid carriers examples include: paraffinic or naphthenic hydrocarbons, such as kerosine, mineral oil, spindle oil and white oil; aromatic hydrocarbons, such as benzene, toluene, xylene, ethylbenzene, cumene and methylnaphthalene; chlorinated hydrocarbons, such as carbon tetrachloride, chloroform, trichloroethylene, monochlorobenzene and o-chlorotoluene; ethers, such as dioxane and tetrahydrofuran; ketones, such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone and isophorone; esters, such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate and diethyl succinate; alcohols, such as
- the fungicidal compositions of the present invention may contain surface active agents to emulsify, disperse, wet, spread, bind, control disintegration of, improve fluidity of or rust-proof the fungicidal composition or to stabilize the active compound; although any of the conventional classes of surface active agent, be they non-ionic, anionic, cationic or amphoteric, may be employed, we prefer to employ non-ionic and/or anionic surface active agents.
- non-ionic surface active agents are: the polymerization adducts of ethylene oxide with higher alcohols, such as lauryl alcohol, stearyl alcohol or oleyl alcohol; the polymerization adducts of ethylene oxide with alkylphenols, such as isooctylphenol or nonylphenol; the polymerization adducts of ethylene oxide with alkylnaphthols, such as butylnaphthol or octylnaphthol; the polymerization adducts of ethylene oxide with higher fatty acids, such as palmitic acid, stearic acid or oleic acid; the polymerization adducts of ethylene oxide with mono- or di-alkylphosphoric acids, such as stearylphosphoric acid or dilaurylphosphoric acid; the polymerization adducts of ethylene oxide with amines, such as dodecylamine; the polymerization adducts of ethylene
- alkyl sulphate salts such as sodium lauryl sulphate or oleyl sulphate amine salt
- alkyl sulphonate salts such as sodium dioctyl sulphosuccinate or sodium 2-ethylhexene sulphonate
- aryl sulphonate salts such as sodium isopropylnaphthalene sulphonate, sodium methylenebisnaphthalene sulphonate, sodium ligninsulphonate or sodium dodecylbenzene sulphonate.
- the agricultural fungicidal compositions of the present invention may be used in combination with high molecular weight compounds or other auxiliary agents, such as casein, gelatin, albumin, glue, sodium alginate, carboxymethylcellulose, methylcellulose, hydroxyethylcellulose or polyvinyl alcohol, in order to improve the properties and/or to increase the biological effect of the composition of the invention.
- high molecular weight compounds or other auxiliary agents such as casein, gelatin, albumin, glue, sodium alginate, carboxymethylcellulose, methylcellulose, hydroxyethylcellulose or polyvinyl alcohol, in order to improve the properties and/or to increase the biological effect of the composition of the invention.
- the fungicidal composition of the present invention may contain the compound of the invention in an amount of from 0.1 to 99% by weight, based upon the weight of the composition, although the precise amount of active ingredient in the composition will, naturally, depend upon the form of the composition, the manner in which it is to be applied and on whether or not the composition contains any other active ingredient.
- dusts may conveniently contain from 1 to 25% by weight of the compound of formula (I), the remainder being a solid carrier.
- Wettable powders may conveniently contain, for example, from 25 to 90% by weight of the compound (I), the remainder being a solid carrier and a dispersing and wetting agent, if required, together with a protective colloid agent, a thixotropic agent and an anti-foaming agent.
- Granules may conveniently contain from 1 to 35% by weight of the compound of formula (I), a major portion of the remainder being a solid carrier.
- the active compound is homogeneously admixed with the solid carrier or is adhered to or adsorbed onto the carrier surface; the diameter of each granule is preferably from 0.2 to 1.5 mm.
- Emulsifiable concentrates may conveniently contain, for example, from 5 to 50% by weight of the compound of formula (I) and from 5 to 20% by weight of an emulsifying agent, the remainder being a liquid carrier, together with, if required, a corrosion inhibitor.
- the fungicidal compositions of the present invention may-be applied to a paddy or upland (dry) field in an amount of from 1 to 5000 g, more preferably from 10 to 1000 g, of the compound of formula (I) per 10 ares for pre- or post- emergence fungicidal activity; they may be applied by foliage spraying, soil drenching, spraying onto irrigation water or any other known method.
- the fungicidal composition of the present invention when employed for seed disinfection or coating, may effectively control soil-borne or seed infectious diseases by coating seeds in an amount of from 0.1 to 2%, preferably from 0.2 to 0.5%, by weight of the compound of formula (I), based on the weight of the seed.
- the fungicidal composition of the present invention may additionally contain other fungicides in order to broaden the fungicidal spectrum and, in some cases, a synergistic effect may be observed.
- the composition may also contain plant growth regulators, herbicides, insecticides or fertilizers, as is well known in the art.
- the fungicidal compositions of the present invention may be used together with control agents effective against rice blast, helminthosporium leaf spot, bacterial leaf blight, rice stem borers, planthoppers and/or leafhoppers, to save the labour involved in separate applications.
- control agents effective against rice blast, helminthosporium leaf spot, bacterial leaf blight, rice stem borers, planthoppers and/or leafhoppers to save the labour involved in separate applications.
- a combination of one or more of these additional control agents with the composition of the invention may be employed, depending upon the disease and/or the insect to be controlled and the form of the composition to be employed.
- Examples 1 to 5 illustrate the preparation of compounds of the invention
- Examples 6, 7 and 8 illustrate the preparation of compositions of the invention
- Examples 9,10 and 11 illustrate the biological activity of the compounds. In all of these Examples, all parts are by weight.
- Compound No. 22 70 parts of Compound No. 22 were finely pulverized and 30 parts of clay were then added and mixed in a mixer to form a premix. 10 parts of this premix were uniformly mixed with 60 parts of clay and 30 parts of bentonite in a mixer. The mixture was kneaded with a suitable amount of water in a kneader, extruded through a screen having apertures of diameter 0.8 mm and dried in a draught drier at 50°C. The resulting product was formed into granules by means of a sifter.
- the compound of the invention was employed in the form of a wettable powder, prepared as described in the Example 7, containing 50% by weight of the active compound.
- the pathogenic fungus of damping-off (Rhizoctonia solani) was incubated on rice bran at 28°C for 2 weeks and then homogeneously mixed with soil.
- the soil was placed in a pot having a diameter of 12 cm, and then 20 cucumber seeds of the variety Sagamihanpaku were sown thereon.
- the soil in the pot was then drenched with a test preparation containing one of the active compounds listed in the following Table 1 in a concentration of 250 ppm, at the rate of 3 litres of preparation per square metre of soil.
- the resulting pots were kept in a greenhouse at 25°C for 2 weeks, after which the number of infected seedlings was determined.
- Table 1 The results are summarised in Table 1.
- the number of infected seedlings obtained from this pot is also reported in Table 1.
- Rice seedlings of the variety Koganenishiki at the 4-5 leaf stage were sprayed with a test preparation containing 30 ppm of one of the active compounds listed in Table 2 in a total amount of 50 ml per 3 pots.
- the host plants were left at room temperature for 24 hours, and then 4-5 oat grains, on which the pathogenic fungus of sheath blight (Rhizoctonia solani) had previously been cultured, were placed around the lower part of the stem of each rice plant.
- the plants were then placed in a greenhouse maintained at 25-27°C and, 10 days after introduction of the fungus, were examined for the degree of damage by determining the height of each diseased spot in centimetres. The results are shown in Table 2, in which the heights of the spots are reported as averaged over each group of 3 pots.
- Rice seedlings of the variety Koganenishiki at the 6-7 leaf stage were infected with sheath blight by placing around the lower part of the stem of each seedling 4-5 oat grains on which the pathogenic fungus of rice sheath blight (Rhizoctonia solani) had previously been cultured.
- the host plants were placed in a greenhouse maintained at 25-27°C and then, 3 days after introduction of the fungus (at which time the height of the diseased area was measured), the hosts plants were removed from the greenhouse and each was sprayed with a test preparation containing 100 ppm of one of the active compounds shown in the following Table 3, in a total amount of 50 ml of the preparation per 3 pots.
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (15)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP124974/81 | 1981-08-10 | ||
JP56124974A JPS5826802A (ja) | 1981-08-10 | 1981-08-10 | 農園芸用殺菌剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0072238A1 EP0072238A1 (fr) | 1983-02-16 |
EP0072238B1 true EP0072238B1 (fr) | 1985-11-06 |
Family
ID=14898816
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP82304197A Expired EP0072238B1 (fr) | 1981-08-10 | 1982-08-09 | Dérivés de pyridazinone, leur préparation et leur utilisation dans des compositions pour l'agriculture et le traitement des graines et des plantes |
Country Status (5)
Country | Link |
---|---|
US (1) | US4738961A (fr) |
EP (1) | EP0072238B1 (fr) |
JP (1) | JPS5826802A (fr) |
CA (1) | CA1194874A (fr) |
DE (1) | DE3267294D1 (fr) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9015764D0 (en) * | 1990-07-18 | 1990-09-05 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
ES2131506T3 (es) * | 1990-09-21 | 1999-08-01 | Rohm & Haas | Dihidropiridacinonas y piridacinonas como fungicidas. |
CN1038249C (zh) * | 1991-08-28 | 1998-05-06 | 罗姆和哈斯公司 | 含有二氢哒嗪酮及其相关化合物的杀菌组合物 |
IL115889A0 (en) * | 1994-11-14 | 1996-01-31 | Rohm & Haas | Pyridazinones and their use as fungicides |
US5635494A (en) * | 1995-04-21 | 1997-06-03 | Rohm And Haas Company | Dihydropyridazinones and pyridazinones and their use as fungicides and insecticides |
AU723064B2 (en) * | 1995-08-25 | 2000-08-17 | Dow Agrosciences Llc | Compositions having synergistic fungitoxic effects |
CA2216512A1 (fr) * | 1996-10-11 | 1998-04-11 | Rohm And Haas Company | Dihydropyridazinones et pyridazinones, leur utilisation comme fongicides et insecticides |
US6063781A (en) * | 1999-02-17 | 2000-05-16 | Lai; Hoi Kiong | Pesticidal phenylpyridazinone derivatives |
BR0213586A (pt) * | 2001-09-27 | 2004-10-26 | Monsanto Technology Llc | Composições fungicidas e suas aplicações em agricultura |
DE102005057924A1 (de) * | 2005-12-05 | 2007-06-06 | Merck Patent Gmbh | Pyridazinonderivate |
US20100158992A1 (en) * | 2007-03-15 | 2010-06-24 | Schering Corporation | Piperazine-substituted pyridazinone derivatives useful as glucan synthase inhibitors |
DE102007025718A1 (de) * | 2007-06-01 | 2008-12-04 | Merck Patent Gmbh | Pyridazinonderivate |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2624730A (en) * | 1950-08-16 | 1953-01-06 | Sterling Drug Inc | 6-haloaryl-3-pyridazones |
US2712542A (en) * | 1952-05-14 | 1955-07-05 | Warner Hudnut Inc | New series of 2-(3-pyridazonyl)-acids and their derivatives and method of preparing members of the series |
US2938902A (en) * | 1959-04-24 | 1960-05-31 | American Cyanamid Co | Novel pyridazinones and methods of preparing same |
JPS442990Y1 (fr) * | 1966-04-23 | 1969-02-04 | ||
JPS4413713Y1 (fr) * | 1967-04-26 | 1969-06-09 | ||
DE2006020A1 (en) * | 1970-02-11 | 1971-09-09 | Farbenfabriken Bayer AG, 5090 Le verkusen | 6-oxopyridazinylmethyl thiophosphates, pesticides |
US3658814A (en) * | 1970-03-17 | 1972-04-25 | Sandoz Ag | 2-(omega-chloroalkyl)-6-aryl substituted-4 5-dihydropyridazin(2h)-3-one |
BE752074A (fr) * | 1970-06-16 | 1970-12-16 | Sandoz Sa | Nouveaux derives de la pyridazine, leur preparation et medicaments contenant ces derives |
US3883530A (en) * | 1972-10-20 | 1975-05-13 | Dow Chemical Co | Chlorine substituted methylpyridazines |
JPS5118470A (en) * | 1974-08-07 | 1976-02-14 | Fujitsu Ltd | Paneruhyojisoshino seizoho |
DE2445681A1 (de) * | 1974-09-25 | 1976-04-15 | Lentia Gmbh | Verfahren zur herstellung von 3-phenylpyridazonen |
US4052395A (en) * | 1975-09-11 | 1977-10-04 | Sankyo Company Limited | Agricultural fungicidal compositions containing 6-(substituted phenyl)-pyridazinones and said pyridazinones |
JPS6037101B2 (ja) * | 1977-03-09 | 1985-08-24 | 三共株式会社 | フエニルピリダジノン誘導体の製法 |
US4279908A (en) * | 1979-04-19 | 1981-07-21 | Sankyo Company Limited | Pyridazine derivatives and their use as agricultural fungicides |
JPS6113767A (ja) * | 1984-06-28 | 1986-01-22 | Fujitsu Ltd | 画素密度変換回路 |
US4772450A (en) * | 1984-07-25 | 1988-09-20 | Trw Inc. | Methods of forming powdered metal articles |
JP3602661B2 (ja) * | 1996-08-08 | 2004-12-15 | 株式会社東芝 | オゾン注入装置の制御システム |
-
1981
- 1981-08-10 JP JP56124974A patent/JPS5826802A/ja active Granted
-
1982
- 1982-08-03 US US06/404,870 patent/US4738961A/en not_active Expired - Fee Related
- 1982-08-06 CA CA000408886A patent/CA1194874A/fr not_active Expired
- 1982-08-09 EP EP82304197A patent/EP0072238B1/fr not_active Expired
- 1982-08-09 DE DE8282304197T patent/DE3267294D1/de not_active Expired
Also Published As
Publication number | Publication date |
---|---|
JPS5826802A (ja) | 1983-02-17 |
DE3267294D1 (en) | 1985-12-12 |
CA1194874A (fr) | 1985-10-08 |
EP0072238A1 (fr) | 1983-02-16 |
JPS6361923B2 (fr) | 1988-11-30 |
US4738961A (en) | 1988-04-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA1082105A (fr) | Derive de pyridazinone; emploi comme fongicides pour les plantes cultivees | |
EP0072238B1 (fr) | Dérivés de pyridazinone, leur préparation et leur utilisation dans des compositions pour l'agriculture et le traitement des graines et des plantes | |
US4279908A (en) | Pyridazine derivatives and their use as agricultural fungicides | |
US4562193A (en) | 4-[2-(Di- or trisubstitutedphenoxy)ethyl amino]thienodipyrimidines and insecticidal and acaricidal composition containing said pyrimidines | |
JPS63115861A (ja) | α−イミノカルボン酸アニリドを含有する除草剤ならびに新規なα−イミノカルボン酸アニリドおよびその製造方法 | |
JPH05140126A (ja) | トリアゾール誘導体および除草剤 | |
US4661486A (en) | Pyridazinone derivatives and their use as agricultural fungicides | |
US4119667A (en) | Haloaniline derivatives as plant growth modifiers | |
CA1160236A (fr) | Derives du carbamoyloxyisoxazole, preparation et insecticides les contenant | |
EP0089650B1 (fr) | Procédé de production de dérivés de pyridazinone antifongiques et certains composés nouveaux produits par un tel procédé | |
CA1287352C (fr) | Esters herbicides | |
HU212605B (en) | Selective herbicidal compositions containing salicylic acid derivatives, process for producing the active ingredient and method for weed control | |
US4400199A (en) | Thiolcarbamate compounds and their use as herbicides | |
US4371388A (en) | 3-Substituted aminoalkyl-2-benzothiazolinones as plant growth regulants | |
GB2103610A (en) | Herbicidal compounds derived from N-sulphonyl-aryloxybenamides and the processes for their preparation and use | |
JPS6344122B2 (fr) | ||
EP0318991B1 (fr) | Agents de protection de plantes pour contrôler les champignons | |
EP0118982A1 (fr) | Composés organo-phosphorés de la quinoxalinone, leur production et utilisation | |
US4584376A (en) | 1-heterocyclicthio-1-cyclopropanecarbonitriles as crop protectants | |
JP3066536B2 (ja) | 縮合ヘテロ環誘導体及び除草剤 | |
JPH0463069B2 (fr) | ||
JPS63313758A (ja) | 新規なジフエニルエ−テル誘導体 | |
JPH0532641A (ja) | メルカプトトリアジン誘導体及びそれを有効成分とする除草剤 | |
JP2000119274A (ja) | トリアゾロピリミジン誘導体 | |
JPH0446170A (ja) | 新規なべンゾフラン誘導体及びそれを含有する除草剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Designated state(s): CH DE FR GB IT LI NL |
|
17P | Request for examination filed |
Effective date: 19830523 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Designated state(s): CH DE FR GB IT LI NL |
|
ITF | It: translation for a ep patent filed | ||
REF | Corresponds to: |
Ref document number: 3267294 Country of ref document: DE Date of ref document: 19851212 |
|
ET | Fr: translation filed | ||
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed | ||
ITTA | It: last paid annual fee | ||
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 19980731 Year of fee payment: 17 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19980814 Year of fee payment: 17 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19980817 Year of fee payment: 17 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 19980824 Year of fee payment: 17 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19980827 Year of fee payment: 17 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990809 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990831 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990831 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20000301 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 19990809 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20000428 |
|
NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee |
Effective date: 20000301 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20000601 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |